Drink and Be Merry at These Windy City Watering Holes

The best Chicago bars have a great wine selection, tasty cocktails and, more importantly, local ambience.(Photo: Valentyn Volkov/Shutterstock)

Chicagoans have always been in favor of a good drink. Have a sip at one of these establishments, loved by locals, and merriment is sure to follow.

Webster’s Wine Bar

Created by two consulting agents who decided to quit big business in pursuit of their passion, Webster’s Wine Bar offers an eclectic selection of fine wines and a friendly atmosphere. With over 500 reserve wines stocked, whether you’re stopping in for a glass, a tasting, or a rented event, the laid-back style of this wine bar is sure to be inviting.

M Lounge

A popular martini lounge, this bar has everything it takes for a fun night out. Apart from the long list of martinis, they also offer beer, champagne, wine, whiskey, scotch and more. Sit at the beautifully illuminated bar or pick a comfortable cushioned chair to unwind. Relish the delicious martinis as you listen to live jazz performances every Tuesday and Wednesday night.


Occasionally live musical performances are held here at Glascott’s, Italian crooners belting out Frank Sinatra and Dean Martin standards are typical. A restaurant is connected to the bar, so you can bring your food back to the bar to eat, drink and enjoy the music. The vintage bar has carved wood decorations throughout. The place is nothing too glamorous, but that is the way many locals trying to stay away from the meat-market joints along Halsted like it.

Nicole Newton is a Navigator at the Renaissance Chicago O’Hare Suites Hotel minutes from fabled Wrigley Field.